Supplementary Material (ESI) for Organic & Biomolecular Chemistry This journal is (c) The Royal Society of Chemistry 2003 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 loop_ _publ_author_name 'Mark Rizzacasa' 'Anthony N. Cuzzupe' 'Romina Di Florio' 'Jonathan M. White' _publ_contact_author_name 'Dr Mark Rizzacasa' _publ_contact_author_address ; Chemistry University of Melbourne Parkville Victoria 3010 AUSTRALIA ; _publ_contact_author_email MASR@UNIMELB.EDU.AU _publ_section_title ; Enantiospecific Synthesis of the Phospholipase A2 Inhibitors (-)-Cinatrin C1 and (+)-Cinatrin C3 ; data_jmwmr1 _database_code_CSD 214283 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H36 Ho0 O6' _chemical_formula_weight 360.48 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ho Ho -14.9734 3.7046 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' _cell_length_a 5.7655(3) _cell_length_b 9.7432(4) _cell_length_c 19.3380(10) _cell_angle_alpha 83.041(5) _cell_angle_beta 85.348(6) _cell_angle_gamma 85.954(4) _cell_volume 1072.72(9) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 25 _cell_measurement_theta_max 30 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.6 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.116 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 396 _exptl_absorpt_coefficient_mu 0.663 _exptl_absorpt_correction_type analytical _exptl_absorpt_correction_T_min 0.86 _exptl_absorpt_correction_T_max 0.95 _exptl_absorpt_process_details Shelx-76 _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54180 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Enraf-Nonius CAD4 X-ray Deffractometer' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4048 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0298 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 0 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.31 _diffrn_reflns_theta_max 65.17 _reflns_number_total 4048 _reflns_number_gt 2922 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0455P)^2^+0.1256P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0079(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.1(2) _refine_ls_number_reflns 4048 _refine_ls_number_parameters 468 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0633 _refine_ls_R_factor_gt 0.0398 _refine_ls_wR_factor_ref 0.1033 _refine_ls_wR_factor_gt 0.0909 _refine_ls_goodness_of_fit_ref 1.018 _refine_ls_restrained_S_all 1.018 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.5779(4) 1.0515(2) 0.51138(13) 0.0614(6) Uani 1 1 d . . . O2 O 0.7007(4) 0.9557(2) 0.62047(13) 0.0656(6) Uani 1 1 d . . . O3 O 0.9227(6) 1.2514(3) 0.5139(2) 0.0890(10) Uani 1 1 d . . . O4 O 1.0797(5) 0.8843(3) 0.52354(17) 0.0777(8) Uani 1 1 d . . . O5 O 0.5645(5) 0.7898(3) 0.48229(16) 0.0860(8) Uani 1 1 d . . . O6 O 0.8748(5) 0.8066(3) 0.40555(15) 0.0897(9) Uani 1 1 d . . . C1 C 0.6797(6) 1.0756(3) 0.5723(2) 0.0613(9) Uani 1 1 d . . . H1 H 0.5935 1.1513 0.5942 0.074 Uiso 1 1 calc R . . C2 C 0.9249(6) 1.1132(4) 0.5480(2) 0.0708(10) Uani 1 1 d . . . H2 H 1.0293 1.0988 0.5861 0.085 Uiso 1 1 calc R . . C3 C 0.9916(6) 1.0154(4) 0.4927(2) 0.0678(10) Uani 1 1 d . . . H3 H 1.1057 1.0561 0.4571 0.081 Uiso 1 1 calc R . . C4 C 0.7540(6) 1.0048(4) 0.4607(2) 0.0635(9) Uani 1 1 d . . . C5 C 0.7411(6) 1.1021(4) 0.3928(2) 0.0760(11) Uani 1 1 d . . . H5A H 0.8030 1.1890 0.3996 0.091 Uiso 1 1 calc R . . H5B H 0.8420 1.0620 0.3569 0.091 Uiso 1 1 calc R . . C6 C 0.5010(7) 1.1331(4) 0.3660(2) 0.0770(11) Uani 1 1 d . . . H6A H 0.3989 1.1752 0.4009 0.092 Uiso 1 1 calc R . . H6B H 0.4371 1.0470 0.3586 0.092 Uiso 1 1 calc R . . C7 C 0.5067(8) 1.2294(5) 0.2981(2) 0.0946(13) Uani 1 1 d . . . H7A H 0.5944 1.3083 0.3037 0.114 Uiso 1 1 calc R . . H7B H 0.5897 1.1810 0.2617 0.114 Uiso 1 1 calc R . . C8 C 0.2695(8) 1.2824(5) 0.2742(3) 0.0960(14) Uani 1 1 d . . . H8A H 0.1906 1.3366 0.3090 0.115 Uiso 1 1 calc R . . H8B H 0.1777 1.2037 0.2717 0.115 Uiso 1 1 calc R . . C9 C 0.2778(8) 1.3712(6) 0.2034(2) 0.0996(14) Uani 1 1 d . . . H9A H 0.3764 1.4470 0.2055 0.120 Uiso 1 1 calc R . . H9B H 0.3507 1.3153 0.1685 0.120 Uiso 1 1 calc R . . C10 C 0.0450(9) 1.4308(6) 0.1798(3) 0.1030(15) Uani 1 1 d . . . H10A H -0.0244 1.4913 0.2132 0.124 Uiso 1 1 calc R . . H10B H -0.0570 1.3557 0.1800 0.124 Uiso 1 1 calc R . . C11 C 0.0582(9) 1.5117(6) 0.1077(3) 0.1072(16) Uani 1 1 d . . . H11A H 0.1634 1.5852 0.1074 0.129 Uiso 1 1 calc R . . H11B H 0.1253 1.4504 0.0744 0.129 Uiso 1 1 calc R . . C12 C -0.1708(9) 1.5749(6) 0.0832(2) 0.1065(16) Uani 1 1 d . . . H12A H -0.2353 1.6391 0.1154 0.128 Uiso 1 1 calc R . . H12B H -0.2781 1.5021 0.0850 0.128 Uiso 1 1 calc R . . C13 C -0.1557(10) 1.6506(7) 0.0104(3) 0.1184(18) Uani 1 1 d . . . H13A H -0.0896 1.5865 -0.0216 0.142 Uiso 1 1 calc R . . H13B H -0.0492 1.7238 0.0088 0.142 Uiso 1 1 calc R . . C14 C -0.3856(10) 1.7137(6) -0.0152(3) 0.1185(18) Uani 1 1 d . . . H14A H -0.4506 1.7798 0.0160 0.142 Uiso 1 1 calc R . . H14B H -0.4937 1.6412 -0.0130 0.142 Uiso 1 1 calc R . . C15 C -0.3642(13) 1.7866(8) -0.0892(3) 0.159(3) Uani 1 1 d . . . H15A H -0.2578 1.8601 -0.0913 0.190 Uiso 1 1 calc R . . H15B H -0.2980 1.7210 -0.1204 0.190 Uiso 1 1 calc R . . C16 C -0.5962(15) 1.8478(10) -0.1142(4) 0.196(4) Uani 1 1 d . . . H16A H -0.5727 1.8938 -0.1608 0.294 Uiso 1 1 calc R . . H16B H -0.6623 1.9133 -0.0836 0.294 Uiso 1 1 calc R . . H16C H -0.7004 1.7751 -0.1139 0.294 Uiso 1 1 calc R . . C17 C 0.4841(6) 0.9060(4) 0.6505(2) 0.0759(11) Uani 1 1 d . . . H17A H 0.5127 0.8243 0.6825 0.114 Uiso 1 1 calc R . . H17B H 0.3938 0.8840 0.6142 0.114 Uiso 1 1 calc R . . H17C H 0.3999 0.9761 0.6750 0.114 Uiso 1 1 calc R . . C18 C 0.7159(6) 0.8566(4) 0.4517(2) 0.0676(10) Uani 1 1 d . . . C19 C 0.8814(10) 0.6588(5) 0.4021(3) 0.1157(18) Uani 1 1 d . . . H19A H 1.0002 0.6339 0.3673 0.174 Uiso 1 1 calc R . . H19B H 0.7328 0.6341 0.3899 0.174 Uiso 1 1 calc R . . H19C H 0.9154 0.6103 0.4467 0.174 Uiso 1 1 calc R . . O1' O 1.2791(4) 0.4787(2) 0.66222(14) 0.0688(7) Uani 1 1 d . . . O2' O 1.1578(4) 0.4852(2) 0.54908(15) 0.0704(7) Uani 1 1 d . . . O3' O 0.9841(5) 0.7304(3) 0.67017(17) 0.0834(8) Uani 1 1 d . . . O4' O 0.7621(4) 0.4040(3) 0.64471(16) 0.0757(8) Uani 1 1 d . . . O5' O 1.2208(5) 0.2054(3) 0.67827(17) 0.0959(9) Uani 1 1 d . . . O6' O 0.9374(5) 0.2252(3) 0.76288(16) 0.0871(8) Uani 1 1 d . . . C1' C 1.1897(6) 0.5621(3) 0.6026(2) 0.0659(10) Uani 1 1 d . . . H1' H 1.2923 0.6371 0.5860 0.079 Uiso 1 1 calc R . . C2' C 0.9549(6) 0.6205(4) 0.6304(2) 0.0701(10) Uani 1 1 d . . . H2' H 0.8502 0.6486 0.5930 0.084 Uiso 1 1 calc R . . C3' C 0.8672(5) 0.4996(3) 0.6805(2) 0.0650(10) Uani 1 1 d . . . H3' H 0.7589 0.5324 0.7175 0.078 Uiso 1 1 calc R . . C4' C 1.0925(5) 0.4314(4) 0.7105(2) 0.0620(9) Uani 1 1 d . . . C5' C 1.1295(7) 0.4721(5) 0.7824(2) 0.0842(12) Uani 1 1 d . . . H5'1 H 1.1399 0.5716 0.7787 0.101 Uiso 1 1 calc R . . H5'2 H 0.9952 0.4483 0.8140 0.101 Uiso 1 1 calc R . . C6' C 1.3486(9) 0.4013(8) 0.8132(3) 0.129(2) Uani 1 1 d . . . H6'1 H 1.3754 0.3117 0.7958 0.154 Uiso 1 1 calc R . . H6'2 H 1.4790 0.4557 0.7947 0.154 Uiso 1 1 calc R . . C7' C 1.3542(11) 0.3801(9) 0.8853(4) 0.159(3) Uani 1 1 d . . . H7'1 H 1.2247 0.3247 0.9035 0.191 Uiso 1 1 calc R . . H7'2 H 1.3246 0.4696 0.9025 0.191 Uiso 1 1 calc R . . C8' C 1.5702(12) 0.3121(11) 0.9169(4) 0.177(3) Uani 1 1 d . . . H8'1 H 1.6414 0.2501 0.8844 0.212 Uiso 1 1 calc R . . H8'2 H 1.6770 0.3846 0.9172 0.212 Uiso 1 1 calc R . . C9' C 1.5659(16) 0.2413(10) 0.9792(5) 0.195(4) Uani 1 1 d . . . H9'1 H 1.4605 0.1678 0.9797 0.234 Uiso 1 1 calc R . . H9'2 H 1.4980 0.3025 1.0125 0.234 Uiso 1 1 calc R . . C10' C 1.7948(17) 0.1757(13) 1.0061(5) 0.191(4) Uani 1 1 d . . . H10C H 1.8621 0.1155 0.9724 0.229 Uiso 1 1 calc R . . H10D H 1.8993 0.2498 1.0053 0.229 Uiso 1 1 calc R . . C11' C 1.7991(19) 0.1030(12) 1.0689(7) 0.214(4) Uani 1 1 d . . . H11C H 1.6921 0.0301 1.0700 0.257 Uiso 1 1 calc R . . H11D H 1.7340 0.1639 1.1026 0.257 Uiso 1 1 calc R . . C12' C 2.0246(17) 0.0355(12) 1.0957(6) 0.190(4) Uani 1 1 d . . . H12C H 2.0905 -0.0252 1.0620 0.228 Uiso 1 1 calc R . . H12D H 2.1314 0.1083 1.0951 0.228 Uiso 1 1 calc R . . C13' C 2.025(2) -0.0389(14) 1.1595(7) 0.224(4) Uani 1 1 d . . . H13C H 1.9181 -0.1116 1.1603 0.269 Uiso 1 1 calc R . . H13D H 1.9605 0.0218 1.1934 0.269 Uiso 1 1 calc R . . C14' C 2.252(2) -0.1060(12) 1.1852(6) 0.192(4) Uani 1 1 d . . . H14C H 2.3190 -0.1657 1.1511 0.231 Uiso 1 1 calc R . . H14D H 2.3583 -0.0335 1.1859 0.231 Uiso 1 1 calc R . . C15' C 2.243(3) -0.1802(17) 1.2473(8) 0.268(6) Uani 1 1 d . . . H15C H 2.1373 -0.2529 1.2464 0.322 Uiso 1 1 calc R . . H15D H 2.1749 -0.1206 1.2813 0.322 Uiso 1 1 calc R . . C16' C 2.4566(19) -0.2437(13) 1.2724(6) 0.216(4) Uani 1 1 d . . . H16D H 2.4273 -0.2882 1.3191 0.324 Uiso 1 1 calc R . . H16E H 2.5666 -0.1742 1.2725 0.324 Uiso 1 1 calc R . . H16F H 2.5190 -0.3113 1.2426 0.324 Uiso 1 1 calc R . . C17' C 1.3685(6) 0.4394(4) 0.5120(2) 0.0855(12) Uani 1 1 d . . . H17D H 1.3314 0.3866 0.4760 0.128 Uiso 1 1 calc R . . H17E H 1.4648 0.3826 0.5438 0.128 Uiso 1 1 calc R . . H17F H 1.4506 0.5183 0.4913 0.128 Uiso 1 1 calc R . . C18' C 1.0950(6) 0.2753(4) 0.7135(2) 0.0691(10) Uani 1 1 d . . . C19' C 0.9109(11) 0.0778(5) 0.7684(3) 0.1196(18) Uani 1 1 d . . . H19D H 0.7962 0.0523 0.8057 0.179 Uiso 1 1 calc R . . H19E H 1.0573 0.0288 0.7779 0.179 Uiso 1 1 calc R . . H19F H 0.8614 0.0544 0.7253 0.179 Uiso 1 1 calc R . . HO3 H 0.924(10) 1.294(5) 0.539(3) 0.09(2) Uiso 1 1 d . . . HO3' H 0.950(12) 0.808(7) 0.639(3) 0.16(3) Uiso 1 1 d . . . H4' H 0.614(9) 0.411(4) 0.654(2) 0.093(15) Uiso 1 1 d . . . H4 H 1.213(10) 0.874(5) 0.507(3) 0.12(2) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0382(12) 0.0671(14) 0.0783(16) -0.0085(12) 0.0011(12) -0.0044(10) O2 0.0445(12) 0.0625(14) 0.0871(17) -0.0030(12) -0.0025(12) 0.0022(10) O3 0.082(2) 0.0656(19) 0.122(3) -0.0089(19) -0.0048(19) -0.0237(16) O4 0.0386(14) 0.0766(17) 0.115(2) -0.0070(15) 0.0008(15) 0.0040(12) O5 0.0619(16) 0.0738(16) 0.123(2) -0.0190(15) 0.0118(16) -0.0194(14) O6 0.0722(18) 0.090(2) 0.108(2) -0.0310(16) 0.0186(17) -0.0074(15) C1 0.0481(18) 0.0526(19) 0.083(3) -0.0104(18) -0.0041(19) 0.0008(15) C2 0.052(2) 0.063(2) 0.097(3) -0.004(2) -0.009(2) -0.0121(17) C3 0.0364(18) 0.070(2) 0.096(3) -0.006(2) 0.0000(18) -0.0086(16) C4 0.0377(18) 0.067(2) 0.085(3) -0.0091(19) 0.0034(18) -0.0067(15) C5 0.050(2) 0.088(3) 0.087(3) -0.001(2) 0.0041(19) -0.0097(19) C6 0.060(2) 0.087(3) 0.081(3) 0.002(2) -0.001(2) -0.014(2) C7 0.067(3) 0.123(4) 0.087(3) 0.013(3) 0.000(2) -0.010(2) C8 0.074(3) 0.119(3) 0.089(3) 0.013(3) -0.004(2) -0.007(3) C9 0.077(3) 0.130(4) 0.086(3) 0.013(3) -0.004(2) -0.013(3) C10 0.079(3) 0.133(4) 0.091(3) 0.017(3) -0.009(2) -0.011(3) C11 0.089(3) 0.145(4) 0.080(3) 0.020(3) -0.007(3) -0.016(3) C12 0.089(3) 0.146(4) 0.078(3) 0.014(3) -0.008(3) -0.008(3) C13 0.099(4) 0.168(5) 0.080(3) 0.022(3) -0.009(3) -0.015(4) C14 0.100(4) 0.161(5) 0.088(3) 0.020(3) -0.014(3) -0.015(4) C15 0.127(5) 0.226(8) 0.107(4) 0.061(5) -0.030(4) -0.025(5) C16 0.160(7) 0.263(10) 0.146(6) 0.076(6) -0.045(6) -0.018(7) C17 0.052(2) 0.069(2) 0.101(3) 0.003(2) 0.002(2) 0.0029(17) C18 0.045(2) 0.079(2) 0.079(3) -0.015(2) -0.0011(19) -0.0058(19) C19 0.119(4) 0.100(4) 0.133(4) -0.053(3) 0.008(4) 0.007(3) O1' 0.0317(12) 0.0730(15) 0.0978(18) 0.0027(14) -0.0056(12) 0.0045(10) O2' 0.0424(12) 0.0679(14) 0.1008(19) -0.0101(14) -0.0040(13) -0.0047(11) O3' 0.0682(16) 0.0578(15) 0.125(2) -0.0159(17) -0.0105(16) 0.0060(13) O4' 0.0342(13) 0.0735(16) 0.120(2) -0.0133(14) -0.0097(14) -0.0042(12) O5' 0.0805(19) 0.0707(16) 0.128(2) -0.0073(16) 0.0177(18) 0.0198(15) O6' 0.0823(19) 0.0730(17) 0.102(2) -0.0003(14) 0.0093(17) -0.0081(15) C1' 0.0440(19) 0.0481(19) 0.105(3) -0.003(2) -0.010(2) -0.0032(15) C2' 0.0451(19) 0.060(2) 0.105(3) -0.010(2) -0.0125(19) 0.0068(16) C3' 0.0332(17) 0.058(2) 0.102(3) -0.010(2) -0.0034(18) 0.0044(15) C4' 0.0305(16) 0.062(2) 0.092(3) -0.0072(18) -0.0035(17) 0.0032(14) C5' 0.057(2) 0.097(3) 0.100(3) -0.020(2) -0.002(2) -0.006(2) C6' 0.070(3) 0.216(7) 0.103(4) -0.030(4) -0.030(3) 0.014(4) C7' 0.094(4) 0.232(8) 0.136(6) 0.030(5) -0.014(4) 0.010(5) C8' 0.100(5) 0.300(11) 0.123(5) 0.007(6) -0.023(4) 0.010(6) C9' 0.131(7) 0.257(10) 0.171(8) 0.052(7) 0.002(6) 0.018(6) C10' 0.155(8) 0.261(11) 0.150(7) 0.010(7) -0.032(6) -0.008(7) C11' 0.152(9) 0.241(10) 0.239(12) 0.017(9) -0.015(9) -0.016(7) C12' 0.140(7) 0.243(11) 0.177(8) 0.024(7) -0.021(7) -0.008(7) C13' 0.172(10) 0.237(11) 0.257(14) -0.013(10) -0.006(10) -0.016(9) C14' 0.184(10) 0.222(10) 0.161(8) 0.009(7) 0.001(8) -0.013(8) C15' 0.196(13) 0.342(19) 0.257(16) -0.001(14) 0.012(12) -0.040(13) C16' 0.148(8) 0.294(13) 0.208(10) -0.032(8) -0.025(8) -0.009(9) C17' 0.052(2) 0.083(3) 0.120(4) -0.014(2) 0.006(2) -0.005(2) C18' 0.0441(19) 0.070(2) 0.089(3) 0.000(2) -0.005(2) 0.0108(18) C19' 0.144(5) 0.079(3) 0.130(4) 0.015(3) 0.007(4) -0.030(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.409(4) . ? O1 C4 1.442(4) . ? O2 C1 1.407(4) . ? O2 C17 1.425(4) . ? O3 C2 1.425(4) . ? O3 HO3 0.68(5) . ? O4 C3 1.421(5) . ? O4 H4 0.82(6) . ? O5 C18 1.199(4) . ? O6 C18 1.336(4) . ? O6 C19 1.448(5) . ? C1 C2 1.509(5) . ? C1 H1 0.9800 . ? C2 C3 1.527(5) . ? C2 H2 0.9800 . ? C3 C4 1.563(5) . ? C3 H3 0.9800 . ? C4 C18 1.508(5) . ? C4 C5 1.527(5) . ? C5 C6 1.515(6) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 C7 1.518(5) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.515(6) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.527(6) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C10 1.507(7) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C11 1.515(6) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C12 1.504(7) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 C13 1.508(6) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C14 1.515(7) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 C15 1.519(7) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 C16 1.517(10) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? O1' C4' 1.430(4) . ? O1' C1' 1.437(4) . ? O2' C1' 1.381(5) . ? O2' C17' 1.431(4) . ? O3' C2' 1.419(5) . ? O3' HO3' 0.93(6) . ? O4' C3' 1.420(4) . ? O4' H4' 0.86(5) . ? O5' C18' 1.190(4) . ? O6' C18' 1.336(5) . ? O6' C19' 1.445(5) . ? C1' C2' 1.514(5) . ? C1' H1' 0.9800 . ? C2' C3' 1.520(5) . ? C2' H2' 0.9800 . ? C3' C4' 1.540(5) . ? C3' H3' 0.9800 . ? C4' C18' 1.514(5) . ? C4' C5' 1.526(5) . ? C5' C6' 1.525(7) . ? C5' H5'1 0.9700 . ? C5' H5'2 0.9700 . ? C6' C7' 1.388(8) . ? C6' H6'1 0.9700 . ? C6' H6'2 0.9700 . ? C7' C8' 1.507(9) . ? C7' H7'1 0.9700 . ? C7' H7'2 0.9700 . ? C8' C9' 1.313(9) . ? C8' H8'1 0.9700 . ? C8' H8'2 0.9700 . ? C9' C10' 1.527(12) . ? C9' H9'1 0.9700 . ? C9' H9'2 0.9700 . ? C10' C11' 1.330(11) . ? C10' H10C 0.9700 . ? C10' H10D 0.9700 . ? C11' C12' 1.516(12) . ? C11' H11C 0.9700 . ? C11' H11D 0.9700 . ? C12' C13' 1.353(12) . ? C12' H12C 0.9700 . ? C12' H12D 0.9700 . ? C13' C14' 1.513(15) . ? C13' H13C 0.9700 . ? C13' H13D 0.9700 . ? C14' C15' 1.325(14) . ? C14' H14C 0.9700 . ? C14' H14D 0.9700 . ? C15' C16' 1.431(16) . ? C15' H15C 0.9700 . ? C15' H15D 0.9700 . ? C16' H16D 0.9600 . ? C16' H16E 0.9600 . ? C16' H16F 0.9600 . ? C17' H17D 0.9600 . ? C17' H17E 0.9600 . ? C17' H17F 0.9600 . ? C19' H19D 0.9600 . ? C19' H19E 0.9600 . ? C19' H19F 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O1 C4 110.5(3) . . ? C1 O2 C17 114.4(3) . . ? C2 O3 HO3 107(5) . . ? C3 O4 H4 106(4) . . ? C18 O6 C19 116.2(3) . . ? O2 C1 O1 112.7(3) . . ? O2 C1 C2 106.4(3) . . ? O1 C1 C2 105.1(3) . . ? O2 C1 H1 110.8 . . ? O1 C1 H1 110.8 . . ? C2 C1 H1 110.8 . . ? O3 C2 C1 110.1(3) . . ? O3 C2 C3 107.7(3) . . ? C1 C2 C3 102.1(3) . . ? O3 C2 H2 112.1 . . ? C1 C2 H2 112.1 . . ? C3 C2 H2 112.1 . . ? O4 C3 C2 111.0(3) . . ? O4 C3 C4 111.6(3) . . ? C2 C3 C4 102.3(3) . . ? O4 C3 H3 110.6 . . ? C2 C3 H3 110.6 . . ? C4 C3 H3 110.6 . . ? O1 C4 C18 108.6(3) . . ? O1 C4 C5 108.7(3) . . ? C18 C4 C5 112.9(3) . . ? O1 C4 C3 105.3(3) . . ? C18 C4 C3 110.8(3) . . ? C5 C4 C3 110.1(3) . . ? C6 C5 C4 116.1(3) . . ? C6 C5 H5A 108.2 . . ? C4 C5 H5A 108.2 . . ? C6 C5 H5B 108.2 . . ? C4 C5 H5B 108.2 . . ? H5A C5 H5B 107.4 . . ? C5 C6 C7 112.1(3) . . ? C5 C6 H6A 109.2 . . ? C7 C6 H6A 109.2 . . ? C5 C6 H6B 109.2 . . ? C7 C6 H6B 109.2 . . ? H6A C6 H6B 107.9 . . ? C8 C7 C6 114.8(3) . . ? C8 C7 H7A 108.6 . . ? C6 C7 H7A 108.6 . . ? C8 C7 H7B 108.6 . . ? C6 C7 H7B 108.6 . . ? H7A C7 H7B 107.5 . . ? C7 C8 C9 114.2(4) . . ? C7 C8 H8A 108.7 . . ? C9 C8 H8A 108.7 . . ? C7 C8 H8B 108.7 . . ? C9 C8 H8B 108.7 . . ? H8A C8 H8B 107.6 . . ? C10 C9 C8 115.4(4) . . ? C10 C9 H9A 108.4 . . ? C8 C9 H9A 108.4 . . ? C10 C9 H9B 108.4 . . ? C8 C9 H9B 108.4 . . ? H9A C9 H9B 107.5 . . ? C9 C10 C11 114.0(4) . . ? C9 C10 H10A 108.8 . . ? C11 C10 H10A 108.8 . . ? C9 C10 H10B 108.8 . . ? C11 C10 H10B 108.8 . . ? H10A C10 H10B 107.6 . . ? C12 C11 C10 115.3(4) . . ? C12 C11 H11A 108.5 . . ? C10 C11 H11A 108.5 . . ? C12 C11 H11B 108.5 . . ? C10 C11 H11B 108.5 . . ? H11A C11 H11B 107.5 . . ? C11 C12 C13 114.5(4) . . ? C11 C12 H12A 108.6 . . ? C13 C12 H12A 108.6 . . ? C11 C12 H12B 108.6 . . ? C13 C12 H12B 108.6 . . ? H12A C12 H12B 107.6 . . ? C12 C13 C14 115.1(4) . . ? C12 C13 H13A 108.5 . . ? C14 C13 H13A 108.5 . . ? C12 C13 H13B 108.5 . . ? C14 C13 H13B 108.5 . . ? H13A C13 H13B 107.5 . . ? C13 C14 C15 113.5(5) . . ? C13 C14 H14A 108.9 . . ? C15 C14 H14A 108.9 . . ? C13 C14 H14B 108.9 . . ? C15 C14 H14B 108.9 . . ? H14A C14 H14B 107.7 . . ? C16 C15 C14 112.8(6) . . ? C16 C15 H15A 109.0 . . ? C14 C15 H15A 109.0 . . ? C16 C15 H15B 109.0 . . ? C14 C15 H15B 109.0 . . ? H15A C15 H15B 107.8 . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? O2 C17 H17A 109.5 . . ? O2 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? O2 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? O5 C18 O6 123.3(4) . . ? O5 C18 C4 125.1(3) . . ? O6 C18 C4 111.6(3) . . ? O6 C19 H19A 109.5 . . ? O6 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? O6 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C4' O1' C1' 110.6(2) . . ? C1' O2' C17' 114.7(3) . . ? C2' O3' HO3' 102(4) . . ? C3' O4' H4' 109(3) . . ? C18' O6' C19' 116.0(4) . . ? O2' C1' O1' 112.5(3) . . ? O2' C1' C2' 109.1(3) . . ? O1' C1' C2' 103.9(3) . . ? O2' C1' H1' 110.4 . . ? O1' C1' H1' 110.4 . . ? C2' C1' H1' 110.4 . . ? O3' C2' C1' 110.3(3) . . ? O3' C2' C3' 107.7(3) . . ? C1' C2' C3' 102.3(3) . . ? O3' C2' H2' 112.1 . . ? C1' C2' H2' 112.1 . . ? C3' C2' H2' 112.1 . . ? O4' C3' C2' 111.4(3) . . ? O4' C3' C4' 109.7(3) . . ? C2' C3' C4' 102.9(3) . . ? O4' C3' H3' 110.9 . . ? C2' C3' H3' 110.9 . . ? C4' C3' H3' 110.9 . . ? O1' C4' C18' 108.2(3) . . ? O1' C4' C5' 109.0(3) . . ? C18' C4' C5' 110.0(3) . . ? O1' C4' C3' 105.9(3) . . ? C18' C4' C3' 110.5(3) . . ? C5' C4' C3' 113.1(3) . . ? C6' C5' C4' 113.1(4) . . ? C6' C5' H5'1 109.0 . . ? C4' C5' H5'1 109.0 . . ? C6' C5' H5'2 109.0 . . ? C4' C5' H5'2 109.0 . . ? H5'1 C5' H5'2 107.8 . . ? C7' C6' C5' 118.4(5) . . ? C7' C6' H6'1 107.7 . . ? C5' C6' H6'1 107.7 . . ? C7' C6' H6'2 107.7 . . ? C5' C6' H6'2 107.7 . . ? H6'1 C6' H6'2 107.1 . . ? C6' C7' C8' 119.3(6) . . ? C6' C7' H7'1 107.5 . . ? C8' C7' H7'1 107.5 . . ? C6' C7' H7'2 107.5 . . ? C8' C7' H7'2 107.5 . . ? H7'1 C7' H7'2 107.0 . . ? C9' C8' C7' 122.9(7) . . ? C9' C8' H8'1 106.6 . . ? C7' C8' H8'1 106.6 . . ? C9' C8' H8'2 106.6 . . ? C7' C8' H8'2 106.6 . . ? H8'1 C8' H8'2 106.6 . . ? C8' C9' C10' 118.7(8) . . ? C8' C9' H9'1 107.6 . . ? C10' C9' H9'1 107.6 . . ? C8' C9' H9'2 107.6 . . ? C10' C9' H9'2 107.6 . . ? H9'1 C9' H9'2 107.1 . . ? C11' C10' C9' 120.9(9) . . ? C11' C10' H10C 107.1 . . ? C9' C10' H10C 107.1 . . ? C11' C10' H10D 107.1 . . ? C9' C10' H10D 107.1 . . ? H10C C10' H10D 106.8 . . ? C10' C11' C12' 121.4(10) . . ? C10' C11' H11C 107.0 . . ? C12' C11' H11C 107.0 . . ? C10' C11' H11D 107.0 . . ? C12' C11' H11D 107.0 . . ? H11C C11' H11D 106.7 . . ? C13' C12' C11' 120.5(10) . . ? C13' C12' H12C 107.2 . . ? C11' C12' H12C 107.2 . . ? C13' C12' H12D 107.2 . . ? C11' C12' H12D 107.2 . . ? H12C C12' H12D 106.8 . . ? C12' C13' C14' 119.7(11) . . ? C12' C13' H13C 107.4 . . ? C14' C13' H13C 107.4 . . ? C12' C13' H13D 107.4 . . ? C14' C13' H13D 107.4 . . ? H13C C13' H13D 106.9 . . ? C15' C14' C13' 117.5(12) . . ? C15' C14' H14C 107.9 . . ? C13' C14' H14C 107.9 . . ? C15' C14' H14D 107.9 . . ? C13' C14' H14D 107.9 . . ? H14C C14' H14D 107.2 . . ? C14' C15' C16' 118.1(13) . . ? C14' C15' H15C 107.8 . . ? C16' C15' H15C 107.8 . . ? C14' C15' H15D 107.8 . . ? C16' C15' H15D 107.8 . . ? H15C C15' H15D 107.1 . . ? C15' C16' H16D 109.5 . . ? C15' C16' H16E 109.5 . . ? H16D C16' H16E 109.5 . . ? C15' C16' H16F 109.5 . . ? H16D C16' H16F 109.5 . . ? H16E C16' H16F 109.5 . . ? O2' C17' H17D 109.5 . . ? O2' C17' H17E 109.5 . . ? H17D C17' H17E 109.5 . . ? O2' C17' H17F 109.5 . . ? H17D C17' H17F 109.5 . . ? H17E C17' H17F 109.5 . . ? O5' C18' O6' 124.1(4) . . ? O5' C18' C4' 125.7(4) . . ? O6' C18' C4' 110.2(3) . . ? O6' C19' H19D 109.5 . . ? O6' C19' H19E 109.5 . . ? H19D C19' H19E 109.5 . . ? O6' C19' H19F 109.5 . . ? H19D C19' H19F 109.5 . . ? H19E C19' H19F 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C17 O2 C1 O1 -66.7(4) . . . . ? C17 O2 C1 C2 178.7(3) . . . . ? C4 O1 C1 O2 -87.3(3) . . . . ? C4 O1 C1 C2 28.0(3) . . . . ? O2 C1 C2 O3 -164.7(3) . . . . ? O1 C1 C2 O3 75.6(4) . . . . ? O2 C1 C2 C3 81.1(3) . . . . ? O1 C1 C2 C3 -38.6(3) . . . . ? O3 C2 C3 O4 158.6(3) . . . . ? C1 C2 C3 O4 -85.4(3) . . . . ? O3 C2 C3 C4 -82.2(3) . . . . ? C1 C2 C3 C4 33.7(3) . . . . ? C1 O1 C4 C18 113.0(3) . . . . ? C1 O1 C4 C5 -123.8(3) . . . . ? C1 O1 C4 C3 -5.7(3) . . . . ? O4 C3 C4 O1 100.4(3) . . . . ? C2 C3 C4 O1 -18.3(3) . . . . ? O4 C3 C4 C18 -16.8(4) . . . . ? C2 C3 C4 C18 -135.5(3) . . . . ? O4 C3 C4 C5 -142.5(3) . . . . ? C2 C3 C4 C5 98.8(3) . . . . ? O1 C4 C5 C6 -49.0(5) . . . . ? C18 C4 C5 C6 71.5(4) . . . . ? C3 C4 C5 C6 -164.0(3) . . . . ? C4 C5 C6 C7 -179.5(4) . . . . ? C5 C6 C7 C8 -171.0(4) . . . . ? C6 C7 C8 C9 -176.0(4) . . . . ? C7 C8 C9 C10 -177.3(5) . . . . ? C8 C9 C10 C11 -176.8(5) . . . . ? C9 C10 C11 C12 -178.8(5) . . . . ? C10 C11 C12 C13 -177.9(5) . . . . ? C11 C12 C13 C14 179.5(5) . . . . ? C12 C13 C14 C15 -178.9(6) . . . . ? C13 C14 C15 C16 179.4(7) . . . . ? C19 O6 C18 O5 -10.0(6) . . . . ? C19 O6 C18 C4 169.2(4) . . . . ? O1 C4 C18 O5 -0.4(5) . . . . ? C5 C4 C18 O5 -121.1(4) . . . . ? C3 C4 C18 O5 114.8(4) . . . . ? O1 C4 C18 O6 -179.6(3) . . . . ? C5 C4 C18 O6 59.7(4) . . . . ? C3 C4 C18 O6 -64.3(4) . . . . ? C17' O2' C1' O1' -73.3(4) . . . . ? C17' O2' C1' C2' 172.0(3) . . . . ? C4' O1' C1' O2' -91.5(3) . . . . ? C4' O1' C1' C2' 26.3(4) . . . . ? O2' C1' C2' O3' -163.0(3) . . . . ? O1' C1' C2' O3' 76.8(3) . . . . ? O2' C1' C2' C3' 82.7(4) . . . . ? O1' C1' C2' C3' -37.5(3) . . . . ? O3' C2' C3' O4' 160.9(3) . . . . ? C1' C2' C3' O4' -82.9(3) . . . . ? O3' C2' C3' C4' -81.6(3) . . . . ? C1' C2' C3' C4' 34.5(4) . . . . ? C1' O1' C4' C18' 114.5(3) . . . . ? C1' O1' C4' C5' -125.9(3) . . . . ? C1' O1' C4' C3' -4.0(4) . . . . ? O4' C3' C4' O1' 99.0(3) . . . . ? C2' C3' C4' O1' -19.7(4) . . . . ? O4' C3' C4' C18' -17.9(4) . . . . ? C2' C3' C4' C18' -136.6(3) . . . . ? O4' C3' C4' C5' -141.8(3) . . . . ? C2' C3' C4' C5' 99.6(4) . . . . ? O1' C4' C5' C6' -64.3(5) . . . . ? C18' C4' C5' C6' 54.1(5) . . . . ? C3' C4' C5' C6' 178.2(4) . . . . ? C4' C5' C6' C7' -153.0(6) . . . . ? C5' C6' C7' C8' -179.2(7) . . . . ? C6' C7' C8' C9' -153.2(10) . . . . ? C7' C8' C9' C10' 179.6(9) . . . . ? C8' C9' C10' C11' -179.9(12) . . . . ? C9' C10' C11' C12' 179.0(10) . . . . ? C10' C11' C12' C13' -179.6(12) . . . . ? C11' C12' C13' C14' 179.7(11) . . . . ? C12' C13' C14' C15' -178.6(14) . . . . ? C13' C14' C15' C16' -179.7(13) . . . . ? C19' O6' C18' O5' -5.1(6) . . . . ? C19' O6' C18' C4' 176.2(4) . . . . ? O1' C4' C18' O5' -4.6(5) . . . . ? C5' C4' C18' O5' -123.5(4) . . . . ? C3' C4' C18' O5' 110.9(4) . . . . ? O1' C4' C18' O6' 174.1(3) . . . . ? C5' C4' C18' O6' 55.1(4) . . . . ? C3' C4' C18' O6' -70.4(4) . . . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 65.17 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.124 _refine_diff_density_min -0.092 _refine_diff_density_rms 0.024